I'm confused about something similar - if I take money from my Roth IRA that I originally contributed (not earnings), do I still have to report it on my taxes even if I know it's not taxable?

The blank Box 2a on your 1099-R is actually a good sign - it likely means TIAA determined the distribution wasn't taxable, which is why they didn't withhold anything this time. However, you absolutely still need to report this on your tax return even if no taxes are owed. Since you mentioned this is from a rollover you did over a year ago, the key question is whether those were pre-tax or after-tax funds that you rolled over. If you rolled over from a traditional 401(k) or IRA to a Roth (a conversion), you would have paid taxes on that conversion at the time. Any distributions from those converted funds would generally be tax-free as long as it's been more than 5 years since the conversion AND you're over 59½. If the rollover was from another Roth account, then the funds maintain their original character and the 5-year clock from your original Roth IRA applies. Make sure to check Box 7 for the distribution code - that will tell you exactly how the IRS expects this to be treated. You'll likely need to file Form 8606 along with your 1040 to properly report this distribution and show why it's not taxable.

Hey! I'm new to this community and dealing with taxes for the first time too. Reading through all these responses has been really educational - I had no idea there were so many nuances to gambling winnings! Just wanted to say thanks to everyone who took the time to explain the difference between the technical requirements (all gambling income is taxable) versus the practical reality (IRS focuses on documented amounts over $600). It's helpful to see real experiences from people who've been in similar situations. One thing I'm taking away is that it's probably worth keeping better records going forward, even for small amounts, just to build good habits. And it sounds like there are some useful tools mentioned here that could help with tax questions as they come up. Thanks again for making this such a welcoming place to learn about these topics!

Welcome to the community and congrats on your first win! I can totally relate to the confusion - when I first started dealing with taxes, even small things like this seemed overwhelming. From what I've learned (and what everyone here has explained really well), you're in a pretty safe spot with that $20. The key takeaway is that while technically all gambling winnings are taxable, the IRS really focuses their attention on amounts where there's proper documentation - typically $600 and above where you'd receive tax forms. For your situation, you could go either way: report it as "other income" to be completely by-the-book, or just cash it and not worry about it since it's such a small, undocumented amount. Either choice is totally reasonable for a $20 win. The most important thing is that you're thinking about this stuff early! Building good tax habits now will serve you well if you ever hit bigger winnings down the road. And don't worry - we've all been beginners at this tax stuff at some point. The community here is really helpful for learning as you go!

As a newcomer to this community, I'm absolutely amazed by the depth of knowledge and support shared in this thread! Reading through everyone's experiences has been both incredibly helpful and frankly quite alarming about how the IRS handles these situations. I'm still fairly new to managing my own tax responsibilities (just started filing independently last year), and @Ella Cofer's experience is exactly the type of situation that would have left me completely panicked and unsure how to advocate for myself. The fact that you can meticulously follow all the correct procedures - mailing on the deadline, obtaining a proper postmark, even photographing your documentation - yet still face incorrect penalties from agents who seem unfamiliar with basic regulations is truly concerning. @Amara Chukwu, your insider expertise regarding IRC Section 7502 and Treasury Regulation 301.7502-1 is absolutely invaluable! Having those specific legal references from someone who actually worked within the IRS system gives me genuine confidence that legitimate taxpayer protections exist, even when individual agents may not consistently apply them correctly. What really resonates with me throughout this discussion is how it highlights the critical importance of thorough documentation and understanding your rights as a taxpayer. The practical strategies shared here - photographing postmarked envelopes, maintaining detailed records, knowing precisely which regulations to cite during calls - represents essential knowledge that honestly should be standard education for anyone filing taxes, not something discovered through community forums after problems emerge. This thread has convinced me to switch to electronic payments going forward for the peace of mind, but I'm grateful to now understand these mail-in protections exist when needed. Thank you to everyone who contributed their experiences and expertise - this represents exactly the kind of community wisdom that makes navigating complex government systems feel achievable for those of us still learning!

As a newcomer to this community, I'm incredibly grateful for this thread and all the valuable insights shared here! Reading through @Ella Cofer's situation and everyone's responses has been both educational and reassuring. I'm still pretty new to handling my own tax obligations independently, and honestly, this type of IRS dispute would have completely overwhelmed me before reading this discussion. The fact that you can do everything correctly - mail on time, get proper documentation, even take photos as proof - yet still face incorrect penalties from agents who don't understand basic regulations is really eye-opening. @Amara Chukwu, thank you so much for sharing your expertise about IRC Section 7502! Having those specific regulation numbers from someone with actual IRS experience is incredibly valuable. It's unfortunate that taxpayers need to become experts on tax code just to get the agency to follow their own rules, but knowing exactly what to reference makes all the difference. The community support here is amazing - from the practical documentation tips to the service recommendations for getting through IRS phone lines more efficiently. This thread feels like a masterclass in taxpayer advocacy that you just can't get from official publications. I'm definitely switching to electronic payments after reading all this, but it's good to know these mail-in protections exist. @Ella Cofer, I hope you get that penalty completely removed - you clearly followed all the rules and have the documentation to prove it. Don't settle for that $9 compromise when you did everything right!

Have you considered having a tax professional review your return before submitting? For something that seems unusual to you, wouldn't it be worth the peace of mind to have someone verify everything is correct? Many military bases offer free tax preparation services through VITA programs. They could confirm if this refund amount is accurate for your specific situation and explain exactly which credits are generating this refund.

Your refund amount is definitely plausible! With 4 dependents and $27k income, you're hitting the sweet spot for both Child Tax Credit ($8,000 for 4 kids) and Earned Income Credit (potentially $6,000+ at your income level). These are refundable credits, meaning you get them even if you owe no tax. The fact that only $28 was withheld doesn't matter - these credits exist specifically to support working families like yours. Your brother-in-law's situation with 3 kids getting $6k actually supports this - one less child means $2k less in Child Tax Credit. The math checks out!

Thanks everyone for the advice! I decided to file an extension to be safe, but I also called the partnership using that phone service someone mentioned. They confirmed my K-3 will only have minimal information since my investment is small. They actually offered to send me a preliminary version of what my K-3 will look like when it's finalized!

That's great news! Getting a preliminary version of the K-3 is actually the best possible outcome - you'll have all the information you need to complete your return accurately without the stress of guessing or filing amendments later. For future reference, many partnerships will provide preliminary K-3 information if you ask directly, but most investors don't know this is an option. It sounds like you found a really practical solution that gives you the certainty you need while still meeting your filing obligations properly. Hope your final return goes smoothly when you get the official K-3!